331-62-4

Usage

Chemical Properties

Colorless solid

InChI:InChI=1/C8H6FNO/c1-11-8-3-2-6(5-10)4-7(8)9/h2-4H,1H3

Upstream product

• 458-50-4 1-bromo-2-fluoro-4-methoxybenzene 
• 544-92-3 copper(I) cyanide 
• 321-28-8 1-fluoro-2-methoxybenzene 
• 151-50-8 potassium cyanide 
• 67-56-1 methanol 
• 64248-62-0 3,4-Difluorobenzonitrile 
• 874-90-8 4-methoxybenzonitrile 
• 2357-52-0 3-fluoro-4-methoxyphenyl bromide 
• 455-93-6 2-fluoro-1-methoxy-4-nitrobenzene 
• 143-33-9 sodium cyanide 
• 456-49-5 1-fluoro-3-methoxybenzene 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 149507-26-6 3-fluoro-4-methoxy-phenylboronic acid 
• 96047-32-4 3-fluoro-4-methoxybenzyl alcohol 

Downstream Products

• 405-04-9 3-fluoro-4-hydroxybenzonitrile 
• 177662-31-6 3-fluoro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide 
• 350-29-8 3-fluoro-4-hydroxybenzoic acid 
• 247570-27-0 (3-fluoro-4-methoxyphenyl)methanammonium chloride 
• 1370439-28-3 C₁₁H₁₁FN₂OS 
• 1370439-22-7 C₁₁H₁₁FN₂O 
• 586-22-1 1-(3-fluoro-4-methoxyphenyl)propan-1-one 
• 586-16-3 1-(3-fluoro-4-hydroxyphenyl)propan-1-one 
• 3907-15-1 3-fluoro-4-methoxybenzoylchloride 
• 1436427-41-6 (4-(2-chloroethoxy)phenyl)(3-fluoro-4-methoxyphenyl)methanone 
• 1388825-86-2 (4-(2-chloroethoxy)phenyl)(3-fluoro-4-hydroxyphenyl)methanone 
• 872045-88-0 4-(2-bromoethoxy)-3-fluorobenzonitrile 
• 1384869-53-7 4-(2-bromoethoxy)-3-fluorobenzoic acid 
• 1384869-54-8 4-(2-bromoethoxy)-3-fluorobenzoyl chloride 

Relevant academic research and scientific papers

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.

Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis

A mild, aerobic, catalytic process for obtaining nitriles directly from alcohols and aqueous ammonia is described. The reaction proceeds via a dehydrogenation cascade mediated by catalytic CuI, bpy, and TEMPO in the presence of O2. The substrate scope is broad including various functionalized aromatic and aliphatic alcohols. This protocol enabled the one-pot synthesis of various biaryl heterocycles directly from commercially available alcohols.

NOVEL ARYLALKENE DERIVATIVES AND USE THEREOF AS SELECTIVE ESTROGEN RECEPTOR MODULATORS

The invention provides novel ethylene derivatives represented by Formula I, which may be used as selective estrogen receptor modulators (SERMs) and useful in the prophylaxis and/or treatment of estrogen-dependent conditions or conditions.

A general rhodium-catalyzed cyanation of aryl and alkenyl boronic acids

Give me a cyanide: N-cyano-N-phenyl-p-methylbenzenesulfonamide as a cyanation reagent allows the synthesis of aryl(alkenyl) nitriles in good yield under mild conditions (see scheme; cod=cycloocta-1,5-diene). Combination of the procedure with the direct borylation of arenes and hydroboration of alkynes leads to the straightforward synthesis of various nitriles.

SUBSTITUTED NAPHTHYRIDINES AND THEIR USE AS SYK KINASE INHIBITORS

The invention relates to new substituted naphthyridines of formula (1), as well as pharmacologically acceptable salts, diastereomers, enantiomers, racemates, hydrates or solvates thereof, wherein R1 is selected from among -O-R3 or -NR3R4, R3 is C1-6-alkyl which is substituted by R5 and R6 R5 is selected from hydrogen, branched or linear C1-6-alkyl, C2-6-alkenyl, -C1-6-alkylen-O-C1-3-alkyl, C1-3-haloalkyl, R6 is ring X wherein n is either 0 or 1, and Formula (I) is a either a single or a double bond and wherein A, B, D and E are each independently from one another selected from CH2, CH, C, N, NH, O or S and wherein ring X is attached to the molecule either via position A, B, D or E, wherein said ring X may optionally be further substituted by one, two or three residues each selected individually from the group consisting of -oxo, hydroxy, -C1-3-alkyl, -C1-3-haloalkyl, -O-C1-3-alkyl, -C1-3-alkanol and halogen, and wherein R4, R2, R7, R8, R9, R10, R11 and Q may have the meanings as given in claim 1, as well as pharmaceutical compositions containing these compounds.

The element effect and nucleophilicity in nucleophilic aromatic photosubstitution (SNAR*). Local atom effects as mechanistic probes of very fast reactions

(Chemical Equation Presented) Photoreactions of 4-nitroanisole and the 2-halo-4-nitroanisoles (halogen = F, Cl, Br, and I) with the nucleophiles hydroxide ion and pyridine have been investigated quantitatively to extend the findings recently communicated for cyanide ion. The halonitroanisoles on excitation form triplet π,π* states, which undergo substitution of the halogen by nucleophiles. Chemical yields of photoproducts, Stern-Volmer kinetic plots, triplet lifetimes, and triplet yields are reported for the five compounds with the three nucleophiles. Following a standard kinetic treatment, 73 rate constants are determined for elementary reactions of the triplets including quenching and various nucleophilic addition processes. The photoadditions are roughly 14 orders of magnitude faster than thermal counterparts. Rate constants for attack at the fluorine-bearing carbon of triplet 2-fluoro-4-nitroanisole are 2.9 × 109, 1.3 × 109, and 6.3 × 108 M-1 s-1 for cyanide ion, hydroxide ion, and pyridine, respectively. The relative rates for attack at the halogen-bearing carbons for F/Cl/Br/I are 27:1.9:1.9:1 (cyanide ion), 29:2.6:2.4:1 (hydroxide ion), and 39:3.9: 3.5:1 (pyridine), respectively. The relative nucleophilicities vary somewhat with the attack site; they are about 5:2:1 for cyanide ion, hydroxide ion, and pyridine for attack at the halogen-bearing carbons. The trend of the element effect opposes that of aliphatic substitution and elimination but is similar in size and parallel to that of thermal nucleophilic aromatic substitution. Relative nucleophilicities in the photoreactions are also similar to those of comparable but vastly slower thermal reactions. The findings imply that the efficiency-determining step of the halogen photosubstitution is simple formation of a σ-complex through electron-paired bonding within the triplet manifold.

The element effect in nucleophilic aromatic photosubstitution (S N2Ar*)

Photoreactions of 4-nitroanisole and the 2-halo-4-nitroanisoles (halogen == F, Cl, Br, I) with NaCN have been investigated. 4-Nitroanisole gave a novel, stable nitronate ion adduct (74%) with cyanide. For the five compounds, we report product distributions, Stern-Volmer kinetic plots, triplet lifetimes, and triplet yields, which afford rate constants for attack by the cyanide ion. Cyanide attack on the fluoride is diffusion controlled; the relative rates for attack at F, Cl, Br, and I are 27:2:2:1, respectively.

Elemental fluorine. Part 20. Direct fluorination of deactivated aromatic systems using microreactor techniques

Continuous flow microreactor technology has been used for the direct fluorination of a range of deactivated di- and tri-substituted aromatic systems.

New oxabispidine compounds for the treatment of cardiac arrhythmias

There is provided compounds of formula I, wherein R1, R2, R3, R41 to R46, X, Y and Z have meanings given in the description, which compounds are useful in the prophylaxis and in the treatment of arrhythmias, in particular atrial and ventricular arrhythmias.

PROCESS FOR THE PREPARATION OF N,N′- DISUBSTITUTED OXABISPIDINES

There is provided a process for the preparation of a sulfonic acid salt of formula I, or a solvate thereof, which process comprises hydrogenating a sulfonic acid salt of formula II,. or a solvate thereof; in the presence of a solvent system consisting essentially of water, a C3-5 secondary alkyl alcohol and no more than 15% v/v of another organic solvent, wherein the sulfonic acid salt of formula I is optionally, without isolation, converted to a compound of formula IX, or a pharmaceutically-acceptable derivative thereof, wherein R1, R2, R3, R6, R7, R8, A, B and D have meanings given in the description.